It’s not always about the wins. Here’s a loss.
I had my eye on a mid-size townhouse complex, 90s vintage, in a tertiary Midwest market. The rents were at 40% of market—$600 for a townhouse when they should have been much higher. Perfect value-add opportunity.
Made a seven-figure offer with easy terms—rejected. Increased the offer—rejected again. Kept following up, waiting for the right moment. Months later, it finally went under contract… for less than my initial offer.
The reason? The seller liked the other buyer. They were local. The agent told me an in-person offer would have made the difference.
Lesson learned: Numbers don’t always win. Relationships matter. In-person meetings, local connections, and trust-building can beat out better offers. Some sellers care more about who’s buying than what they’re paying.
You can’t win them all, but you can always improve your approach. How many deals have you seen slip away like this?